4 Cubs moves that must be made to block Brewers before 2027 lockout

The overarching theme of the Chicago Cubs' offseason is clear, close the gap with the Milwaukee Brewers. It's a problem that Jed Hoyer has never been able to solve, and 14 games separated the two teams in 2026. Of course, there's also the added insult that is the Milwaukee Brewers being the defending World Series champions.

It's also an awkward time for the Cubs. Their contention window is open, but there's a case to be made that it's already closing. Pete Crow-Armstrong is the clear superstar of the group, but the roster is littered with questions after that.

Alex Bregman is approaching the wrong side of 30, Dansby Swanson's offense is already becoming a liability, Nico Hoerner's inconsistency in 2026 gave the Cubs one red flag they might not be able to fix, and Michael Busch didn't take the expected step forward last season.

Here are 4 moves the Cubs must make before the MLB lockout to close the gap to the Brewers

Given the number of players from the 2026 team that have become free agents, this offseason figures to be a pivotal one for the Cubs. It's a reset, in the sense that they will have a new core in 2027, but there's also going to be the expectation of catching the Brewers, even if that may not be possible. With little time to waste before the lockout, there are the moves that Cubs should make this month with the Brewers in mind.

To be clear, this is not every move the Cubs need to make this offseason, just the moves they should focus on first, making life easier for them once the lockout is over. Note that with the contract predictions, we will be using FanGraphs' median crowdsource projections.

Sign Michael King, contract: Four years, $100 million

It's hard to do the math with the Cubs and Tarik Skubal. Sure the Cubs want Skubal, any team would, but nothing in their spending history suggests they are going to go to the level to top the market for the best starting pitcher available this offseason.

Even with that in mind, the Cubs have to walk away from this offseason with an ace. Anything short of that will provide a certainty that they won't catch the Brewers in 2027. That is where Michael King comes into play, considering he has the ideal combination of keeping the ball on the ground, but also capable of missing bats frequently.

Sign Sonny Gray, contract: Two years, $52 million

In part, this is why it's hard to see the Cubs going after Skubal. For how Jed Hoyer has operated in the past, he prefers multiple bites at the apple. For significantly less than the total money it would require to sign Skubal, the Cubs could add both King and Sonny Gray.

What has made the Brewers' machine operate is that they are a pitching factory. They develop pitchers, and often have a rotation capable of shutting down opposing offenses. Until the Cubs prove they can develop pitching with regular success, they will need to throw money at expected results. For this current free-agent, there are few better options than Gray. Gray posted a 2.72 ERA across 29 starts with the Red Sox in 2026, and would give the Cubs slightly more of an upside than Clay Holmes.

Sign David Peterson, contract: Two years, $22 million

The reality is the Cubs have ran out of pitching when they needed it the most over the last two seasons. They tried to fix that problem at the deadline this past summer, but once the playoffs rolled around, it was a struggle for Craig Counsell to map out his rotation. Injuries certainly played a factor in that, and while they can't be predicted, the more high-quality depth options the Cubs assemble, the better off they will be in October.

For two years, $22 million, the Cubs can do far worse than David Peterson. Even if he isn't as successful in 2027 as he was with the Cubs this year, he still as the floor of being a capable swingman in the bullpen.

Trade for Masataka Yoshida, Boston Red Sox

The Boston Red Sox have a surplus of outfielders, and the expectation is that Masataka Yoshida will be playing elsewhere in 2027. He's in the final year of a five-year deal worth $90 million, and Yoshida would give the Cubs an ideal bridge in the outfielder until Josiah Hartshorn and Kane Kepley are ready.

Yoshida would be a more established option than Matt Shaw or Pedro Ramirez in the outfield, and his arrival could push Shaw closer to being a trade candidate for a cost-controlled pitcher. Outfield may not be the top priority for the Cubs this offseason, but it will need to be addressed.

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